Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. $225 to $289/night

    Pacific Shores B414

    Pacific Shores B414

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $156 to $296/night

    Hale Ono Loa 205

    Hale Ono Loa 205

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  3. $237 to $359/night

    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    3 Bedrooms2.5 BathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  4. $520 to $581/night

    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  5. $1,692 to $2,494/night

    Rainbow Hale Estate

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  6. $359 to $608/night

    Golf Villas G2 at Mauna Lani Resort

    Golf Villas G2 at Mauna Lani Resort

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  7. $200 to $289/night

    Kulakane 211

    Kulakane 211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. $261 to $376/night

    Napili Shores I270

    Napili Shores I270

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $214 to $319/night

    Kihei Akahi C-616

    Kihei Akahi C-616

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  10. $200 to $320/night

    Kahana Reef 107

    Kahana Reef 107

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  11. $240 to $286/night

    Maalaea Banyans 203

    Maalaea Banyans 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $476 to $690/night

    Napili Point A9

    Napili Point A9

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  13. $189 to $290/night

    Papakea D108

    Papakea D108

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $188 to $315/night

    Eldorado L102

    Eldorado L102

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $200 to $316/night

    Kauhale Makai 203

    Kauhale Makai 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. $200 to $299/night

    Kihei Alii Kai A207

    Kihei Alii Kai A207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $159 to $356/night

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $119 to $257/night

    Ocean-View Golf Getaway: Pool & Tennis- Near Beach

    Ocean-View Golf Getaway: Pool & Tennis- Near Beach

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  19. $205 to $276/night

    206

    206

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  20. $161 to $303/night

    New Listing! Ocean-View Apartment w/ Pool & Spa

    New Listing! Ocean-View Apartment w/ Pool & Spa

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $200 to $384/night

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    Unobstructed Oceanfront! 2BR + Loft w/ Lanai, Pool

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  22. $656 to $906/night

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  23. $296 to $356/night

    Maui Banyan #H-308

    Maui Banyan #H-308

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $413 to $528/night

    Maui Kamaole #a-204

    Maui Kamaole #a-204

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  25. $152 to $443/night

    Kaleialoha #215

    Kaleialoha #215

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. $173 to $263/night

    Valley Isle #1104

    Valley Isle #1104

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  27. $133 to $409/night

    Kailua Bay Resort #3301

    Kailua Bay Resort #3301

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. $240 to $353/night

    Hoyochi Nikko #102

    Hoyochi Nikko #102

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  29. $269 to $369/night

    Eldorado K102

    Eldorado K102

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $164 to $502/night

    Kaleialoha #304

    Kaleialoha #304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  31. $329/night

    Turtle Bay Kona Coffee***TA-163265126401 Available 30 nights

    Turtle Bay Kona Coffee***TA-163265126401 Available 30 ni...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  33. $235 to $363/night

    333

    333

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  34. $418 to $891/night

    Noelani 304 3bdrm 2.5 bath

    Noelani 304 3bdrm 2.5 bath

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  35. $297 to $390/night

    Maui Kamaole #C-106

    Maui Kamaole #C-106

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. $252 to $302/night

    Maui Sunset #a-106

    Maui Sunset #a-106

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  37. $270 to $354/night

    Hale Kohea

    Hale Kohea

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  38. $252 to $302/night

    Maui Sunset #a-206

    Maui Sunset #a-206

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  39. $501 to $557/night

    Sands of Kahana 366

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  40. $334 to $444/night

    Sugar Beach #124

    Sugar Beach #124

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  41. $194 to $279/night

    Sea Village 1-205-Oceanfront

    Sea Village 1-205-Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  42. $241 to $279/night

    Maui Vista #1225

    Maui Vista #1225

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  43. $347 to $426/night

    Kauhale Makai #135

    Kauhale Makai #135

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. $220 to $356/night

    Kaleialoha 210

    Kaleialoha 210

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  45. $231/night

    Aina Nalu G102

    Aina Nalu G102

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. $298 to $354/night

    Sands Of Kahana 134

    Sands Of Kahana 134

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  47. $214 to $270/night

    Kahana Sunset B1B

    Kahana Sunset B1B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
  48. $474 to $711/night

    Papakea L405

    Papakea L405

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  49. $283/night

    Turtle Bay Anthurium**TA-155327078401 Available 30 nights

    Turtle Bay Anthurium**TA-155327078401 Available 30 night...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. $218/night

    Turtle Bay North Shore Golf TA-151246848001 Available 30 nights

    Turtle Bay North Shore Golf TA-151246848001 Available 30...

    2 Bedrooms2.5 BathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  51. $191/night

    Turtle Bay Hale Kuilima**TA-114877030401 Available 30 nights

    Turtle Bay Hale Kuilima**TA-114877030401 Available 30 ni...

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  52. $237/night

    Turtle Bay Hale Mokulani***TA-055745536001 Available 30 days

    Turtle Bay Hale Mokulani***TA-055745536001 Available 30 ...

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  53. $237/night

    Turtle Bay Gardenia***TA-197395456001 Available for 30 days

    Turtle Bay Gardenia***TA-197395456001 Available for 30 d...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  54. $161/night

    Turtle Bay Lilikoi**TA-009966796801 Available 30 nights

    Turtle Bay Lilikoi**TA-009966796801 Available 30 nights

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  55. $258 to $409/night

    328

    328

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. $214 to $238/night

    Puamana 21D

    Puamana 21D

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  57. $259 to $428/night

    C4-1 Bedroom Oceanfront

    C4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  58. $436 to $715/night

    Lokelani A203

    Lokelani A203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  59. $259 to $394/night

    Royal Kahana 308

    Royal Kahana 308

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. $362 to $861/night

    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  61. $258 to $340/night

    258

    258

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. $170/night

    Islander on the Beach 259

    Islander on the Beach 259

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  63. $226 to $257/night

    Sealodge G4

    Sealodge G4

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  64. $264 to $299/night

    Hula Hideaway-303

    Hula Hideaway-303

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  65. $318 to $426/night

    Sugar Beach #223

    Sugar Beach #223

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. $200 to $300/night

    Valley Isle 407

    Valley Isle 407

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  67. $276 to $332/night

    Kahana Sunset D7

    Kahana Sunset D7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  68. $186 to $219/night

    Sands Of Kahana 122

    Sands Of Kahana 122

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  69. $197 to $248/night

    Golf Villa 19T4

    Golf Villa 19T4

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool
  70. $506 to $563/night

    Sands Of Kahana 234

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  71. $261 to $326/night

    Maui Parkshore #105

    Maui Parkshore #105

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
  72. $423 to $780/night

    Pele's Last Resort (Holua Kai #29)

    Pele's Last Resort (Holua Kai #29)

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  73. $241 to $312/night

    Valley Isle 110

    Valley Isle 110

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. $164 to $502/night

    Kaleialoha #313

    Kaleialoha #313

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  75. $305 to $390/night

    Maui Sunset #A-408

    Maui Sunset #A-408

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. $278 to $341/night

    Junior Suite Oceanfront #702

    Junior Suite Oceanfront #702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  77. $253 to $311/night

    Leinaala #204

    Leinaala #204

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  78. $309 to $366/night

    Kahana Sunset B6

    Kahana Sunset B6

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pool
  79. $188 to $297/night

    135

    135

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  81. $443 to $1,022/night

    Idyllic 1BR Oceanfront Cottage

    Idyllic 1BR Oceanfront Cottage

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  82. $160 to $266/night

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  83. $237 to $502/night

    Maui Eldorado Condo B102

    Maui Eldorado Condo B102

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. $283/night

    Turtle Bay Aloha Nui Loa***T-090-094-0800-01 Available 30 nights

    Turtle Bay Aloha Nui Loa***T-090-094-0800-01 Available 3...

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  85. $135 to $344/night

    2BR Garden Cottage- Walk to Beach!

    2BR Garden Cottage- Walk to Beach!

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  86. $291 to $438/night

    Kaanapali Royal H303

    Kaanapali Royal H303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  87. $260/night

    Turtle Bay Fazio First Tee 13***NUC 90-TVU-0579

    Turtle Bay Fazio First Tee 13***NUC 90-TVU-0579

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. $188 to $258/night

    111

    111

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  89. $169 to $239/night

    Kona Shores#130

    Kona Shores#130

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. $301 to $350/night

    Keauhou Kona Surf & Racquet Club 3202

    Keauhou Kona Surf & Racquet Club 3202

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  91. $377 to $591/night

    C1-2 Bedroom Oceanfront

    C1-2 Bedroom Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  92. $304 to $467/night

    D10-Beachfront Loft Suite

    D10-Beachfront Loft Suite

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  93. $259 to $428/night

    G5-1 Bedroom Oceanfront

    G5-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  94. $278 to $341/night

    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  95. $235 to $295/night

    Puamana 16C- Hale Makai

    Puamana 16C- Hale Makai

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. $156 to $279/night

    Napili Shores C116

    Napili Shores C116

    Studio BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  97. $229 to $365/night

    Honua Kai Konea 224

    Honua Kai Konea 224

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. $306 to $394/night

    Kahana Sunset C 3

    Kahana Sunset C 3

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  99. $208 to $310/night

    Island Surf 409

    Island Surf 409

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. $282 to $628/night

    Maui Eldorado Condo J206

    Maui Eldorado Condo J206

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION